How to Plan Your First Trip to Italy | A List of My Favorite Cities

There is something truly spectacular, utterly untouchable about Italy. From Rome, Italy’s most ancient and vibrant city, to Siena, an old world gem, and the many places in between, the country offers whatever ones heart desires. You’ve just got to get there to see it for yourself!

Do you have a good amount of time to explore Italy and don’t quite know, this blog post is for you. Italy is vast and unique; each of its top cities has something unique to offer. Below is a list of my favorite cities, in order, so you can decide which one most pulls at your wanderlust strings.

Rome

Rome can feel so significant, and so rich with history, yet modern-feeling and well-maintained.

On some streets, in some moments, Rome feels like a sea of people gliding through the city, head phones in, faces forward; horns honking at one another and drivers moving towards their independent dreams. But turn a corner and you’re suddenly fenced in by tall, colorful homes in a quiet alleyway.

Just outside the noisy streets, kids ride freely on their bikes past us, their family’s laundry hanging out their windows to dry just down the way. You're among friends (though you haven’t met). Kindred spirit

It is to me, the TOP city to visit in Italy a , which is a statement friends of mine have noted is as controversial as the gladiatorial matches held in Rome’s Colosseum in the common era. It’s where you can see some of the most famous pieces of art in existence, where you need no excuses to drink delicious wine and eat with pleasant company by night.

On our journey across Italy, I learned quickly why Rome is one of Europe’s most loved cities. Upon arrival, Rome enveloped me; it gave me a new energy, like breathing in crisp fall air, and jump-started our pulses. Rome woke me back up, gave me new pep in my step, invigorating my senses. Our trip started up again in Rome.

If Rome sounds right to you, check out my post: Rome by Foot

Florence

Florence is the ultimate walking city, with broad pedestrian-friendly avenues, shared by bikers and Vespas. In a way it feels like stepping back in time, traveling about on cobblestone streets. Vespa tours are offered here to get you out of the city – one more busy than I had expected.

In addition to the “city of romance”, Florence is known for two things: the quality of its leather and its gold. Expensive shops and booths were exploding off the streets.

The city center houses Florence’s main cathedral, the Duomo, which dominates the main square and seems to guide the city skyline. Further down the square, just outside the Uffizi Gallery, where the streets are alive with visitors – lined with shops, pizza spots, cafes and vendors. The Academia Gallery houses the famous statue of David.

At night, all feels different.

Florence’s famous bridge, the Ponte Vecchio, hosts the most beautiful sunset views. Musicians play in front of the setting sun, and a crowd of spectators gathers to listen. The street, the Plaza Della Signoria, along with Ponte Vecchio, offer some of the best views of the sunset over the Amo river.

Siena/Tuscany

If you are fortunate to make it to Florence, head to Siena, a hill town guided by the pulse of the clocks, from there. Located about two hours north of Rome about one hour south of Florence, Siena is at the center of Italy’s Tuscany region.

The small town is known for its fan-shaped “Piazza del Campo” and the medieval charm of its buildings; the Piazza del Campo, features the Gothic town hall and the clock tower, built in the 14th century, which looms over the brick-laid plaza.

The city extends out from this center into 17 historic wards. Today, it is a city filled with small shops and pizza spots, but in early centuries, the city was a commerce and trade hot spot, rivaling Florence in wealth and power. But Siena has moved into its own category since then, and is unique in that it hasn’t allowed motor traffic throughout its center since the ’60’s.

If you make it to Siena (and I hope you will), plan to spend a few days there. Rent some Vespas, and explore from there. It is the perfect hideaway/getaway from some of the rush-rush parts of Italy – and the perfect launching point for other worthy visits in Tuscany – Montalcino, Pisa and more.

Are you feeling like a visit to Siena? Here’s what we got up to.

And there it is: there is plenty more I could say about the historic wonder that is Pompeii, the amazing hike views of the Amalfi Coast, and the pure elegance of Venice. For more on these sites, check out some of my other blog posts.

Jenna Hedlund